Potassium Iodide → HCID 19385115, compound

HRID 1753662Notes

Reaction equation

HRID 1753662 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].C1(=O)O[CH2:18][CH2:17][O:16]1.[I-].[K+].CN(C)C=O>C(OCC)(=O)C>[OH:16][CH2:17][CH2:18][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 7303Ethylene carbonateHCID 15731(1,1'-Biphenyl)-2,2'-diol

Product 1

HCID 19385115HCID 19385115, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a 2000 ml 3 neck round bottom equipped with an overhead stirrer, temperature probe, heating mantel was added 2,2′-dihydroxy-biphenyl (500 g, 2.68 mole, 1.0 eq), ethylene carbonate (520.2 g, 5.9 mole, 2.2 eq.), potassium iodide (5 g, 0.03 mole, 0.01 eq.), N,N-dimethyl formamide (DMF) (47 g, 50 ml) and heated to 150° C. The reaction was monitored by GC and after 4 hours the reaction was complete. The reaction was cooled to 40° C., added 1000 ml ethyl acetate and washed 3 times with 500 ml sodium chloride brine. The ethyl acetate was dried over MgSO4, filtered and concentrated in vacuo to recover a dark brown product (736 g, 99%).

Workup

  1. temperaturetemperature probe, heating mantel
  2. temperatureThe reaction was cooled to 40° C.
  3. washwashed 3 times with 500 ml sodium chloride brine
  4. dry with materialThe ethyl acetate was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto recover a dark brown product (736 g, 99%)

Sources & evidence

ORD record
ord-c934d25e45084802ab206ae9f3aa45ea
Source dataset
uspto-grants-2015_10
Patent number
US09164195B2

Reaction notes

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